a) Field of the Invention
This invention relates to novel calixarene derivatives and to the use of such derivatives for sequestration of metals.
b) Description of the Related Art
U.S. Pat. No. 4,882,449 Harris et. al. describes nitrogen-containing calixarene derivatives selected from the groups represented by the formulae I and II: ##STR3## wherein m+n=4, 6 or 8
n=an integer 1-8 PA1 m=an integer 0-7 PA1 x=4, 6 or 8 PA1 R.sup.1 is H, alkyl, aralkyl, alkoxy, aroyl, or alkoyl, PA1 R.sup.4 is unsubstituted or substituted hydrocarbyl, carbonyl or aryl; PA1 R.sup.5 and R.sup.6 (which may be the same or different) are hydrogen, or unsubstituted or substituted hydrocarbyl. PA1 n=0-8 PA1 m'.gtoreq.1/2 (m'+m") PA1 3.ltoreq.m'+m"+n.ltoreq.8 PA1 if n=0, m'+m".gtoreq.4 PA1 R.sup.3 is H, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof and R.sup.3 may be the same or different on each aryl group; PA1 R.sup.1 and R.sup.15 which may be the same or different are H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof; PA1 R.sup.2 is selected from: PA1 n=0-8 PA1 m'.gtoreq.1/2 (m'+m") PA1 3.ltoreq.m'+m"+n.ltoreq.8 PA1 if n=0, m'+m".gtoreq.4 PA1 R.sup.3 is H, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof and R.sup.3 may be the same or different on each aryl group; PA1 R.sup.15 is H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof; PA1 X is selected from ##STR7## wherein R.sup.7 and R.sup.8 which may be the same or different are H or hydrocarbyl (including a cycloaliphatic ring formed by R.sup.7 and R.sup.8 together), aryl, hydrocarbylaryl or a substituted derivative thereof; R.sup.9 is --OH, --NH.sub.2, --NHC(O)NH.sub.2 or --NHAr, wherein Ar is aryl or a substituted derivative thereof, PA1 n' is 0 or 1.
R is aliphatic or aromatic, unsubstituted or substituted, hydrocarbyl containing nitrogen.
That application also describes use of such calixarene derivatives for selectively sequestering transition metals from aqueous mixtures of alkali metals and transition metals.
European Patent Publication No. 0,309,291 (Application No. 88 308 897.3) describes oxacalixarene and calixarene derivatives of the formula III: ##STR4## wherein m'+m"=0-8
R.sup.4 which is H, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, ##STR5## wherein R.sup.5 and R.sup.6 which may be the same or different are H, hydrocarbyl, aryl, hydrocarbylaryl, or a substituted derivative thereof, PA2 --OR.sup.1, wherein R.sup.1 is as defined above, and R.sup.17 which is a residue of a hydrocarbyl, aryl or hydrocarbylaryl group or of a substituted derivative thereof providing a bond to another oxacalixarene or calixarene derivative of formula III wherein R.sup.2 is R.sup.17.
That application also describes use of such compounds for sequestering transition metals such as copper and silver, transition series elements such as manganese, alkaline earth elements such as calcium and magnesium, and Group III elements such as aluminium in addition to alkali metals. However the compounds described therein are not selective in their action in sequestering the said metals and other elements.
U.S. Pat. No. 4,477,377 Izatt et. al., describes the use of calix(8)arene, calix(6)arene or calix(4)arene in selective recovery of cesium ions from mixtures thereof with other metals, particularly alkali metals.
Other nitrogen-containing calixarene derivatives are described by C. D. Gutsche and K. C. Nam in J. Am. Chem. Soc., 1988 110 pages 6153-62.